Identification
NameOseltamivir
Accession NumberDB00198  (APRD01148)
TypeSmall Molecule
GroupsApproved
Description

An acetamido cyclohexene that is a structural homolog of sialic acid and inhibits neuraminidase. [PubChem]

Structure
Thumb
Synonyms
(−)-oseltamivir
1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R-(3alpha,4beta,5alpha))-
Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate
Oseltamivir
oséltamivir
Oseltamivirum
External IDs GS 4104 / GS-4071 ETHYL ESTER / GS-4104 / GS4104 / HSDB 7433 / RO-64-0796 / RO-640796 / RO64-0796
Product Ingredients
IngredientUNIICASInChI KeyDetails
Oseltamivir phosphate4A3O49NGEZ 204255-11-8PGZUMBJQJWIWGJ-ONAKXNSWSA-NDetails
Product Images
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Nat-oseltamivirCapsule75 mgOralNatco Pharma Limited2016-09-29Not applicableCanada
TamifluCapsule75 mg/1OralA S Medication Solutions1999-10-272017-06-20Us
TamifluCapsule75 mg/1OralRebel Distributors1999-10-27Not applicableUs
TamifluCapsule75 mgOralRoche Registration Limited2002-06-20Not applicableEu
TamifluCapsule30 mgOralHoffmann La Roche2008-12-01Not applicableCanada
TamifluPowder, for suspension6 mg/mLOralGenentech, Inc.2013-08-01Not applicableUs
TamifluCapsule45 mgOralRoche Registration Limited2002-06-20Not applicableEu
TamifluPowder, for suspension6 mg/mLOralA S Medication Solutions2013-08-012017-06-20Us
TamifluCapsule45 mg/1OralPhysicians Total Care, Inc.2009-10-30Not applicableUs00004 0801 85 nlmimage10 8e41c70e
TamifluPowder, for suspension12 mg/mLOralDispensing Solutions, Inc.2000-12-14Not applicableUs
TamifluCapsule45 mg/1OralGenentech, Inc.1999-10-27Not applicableUs
TamifluCapsule75 mg/1OralRemedy Repack2012-10-31Not applicableUs
TamifluPowder, for suspension6 mg/mLOralRebel Distributors2011-07-11Not applicableUs
TamifluPowder, for suspension12 mg/mlOralRoche Registration Limited2002-06-20Not applicableEu
TamifluCapsule45 mgOralHoffmann La Roche2008-12-08Not applicableCanada
TamifluPowder, for suspension6 mg/mLOralPhysicians Total Care, Inc.2011-11-03Not applicableUs
TamifluPowder, for suspension6 mg/mlOralRoche Registration Limited2002-06-20Not applicableEu
TamifluCapsule30 mg/1OralGenentech, Inc.1999-10-27Not applicableUs00004 0802 85 nlmimage10 293f949c
TamifluPowder, for suspension6 mgOralHoffmann La Roche2012-09-10Not applicableCanada
TamifluCapsule75 mg/1OralA S Medication Solutions1999-10-272017-06-20Us
TamifluCapsule75 mg/1OralPhysicians Total Care, Inc.2002-10-28Not applicableUs00004 0800 85 nlmimage10 491e24c1
TamifluCapsule30 mgOralRoche Registration Limited2002-06-20Not applicableEu
TamifluCapsule75 mg/1OralDispensing Solutions, Inc.1999-10-27Not applicableUs
TamifluCapsule75 mg/1OralGenentech, Inc.1999-10-27Not applicableUs
Tamiflu Capsule 75mgCapsule75 mgOralHoffmann La Roche1999-12-23Not applicableCanada
Tamiflu Oral SuspensionPowder, for suspension12 mgOralHoffmann La Roche2003-12-192013-12-12Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EbilfuminCapsule30 mgOralActavis Group Ptc Ehf.2014-05-22Not applicableEu
EbilfuminCapsule45 mgOralActavis Group Ptc Ehf.2014-05-22Not applicableEu
EbilfuminCapsule30 mgOralActavis Group Ptc Ehf.2014-05-22Not applicableEu
EbilfuminCapsule75 mgOralActavis Group Ptc Ehf.2014-05-22Not applicableEu
EbilfuminCapsule45 mgOralActavis Group Ptc Ehf.2014-05-22Not applicableEu
EbilfuminCapsule75 mgOralActavis Group Ptc Ehf.2014-05-22Not applicableEu
Oseltamivir PhosphateCapsule75 mg/1OralZydus Pharmaceuticals Usa, Inc.2017-02-24Not applicableUs
Oseltamivir PhosphateCapsule75 mg/1OralAlvogen, Inc.2016-12-12Not applicableUs
Oseltamivir PhosphateCapsule30 mg/1OralAmneal Pharmaceuticals2017-05-21Not applicableUs
Oseltamivir PhosphateCapsule45 mg/1OralZydus Pharmaceuticals Usa, Inc.2017-02-24Not applicableUs
Oseltamivir PhosphateCapsule30 mg/1OralAlvogen, Inc.2016-12-12Not applicableUs
Oseltamivir PhosphateCapsule75 mg/1OralNucare Pharmaceuticals, Inc.2016-12-12Not applicableUs
Oseltamivir PhosphateCapsule75 mg/1OralA S Medication Solutions2016-12-122017-06-20Us
Oseltamivir PhosphateCapsule45 mg/1OralAmneal Pharmaceuticals2017-05-21Not applicableUs
Oseltamivir PhosphateCapsule45 mg/1OralAlvogen, Inc.2016-12-12Not applicableUs
Oseltamivir PhosphateCapsule30 mg/1OralZydus Pharmaceuticals Usa, Inc.2017-02-24Not applicableUs
Oseltamivir PhosphateCapsule75 mg/1OralAidarex Pharmaceuticals LLC2016-12-12Not applicableUs
Oseltamivir PhosphateCapsule75 mg/1OralAmneal Pharmaceuticals2017-05-21Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AgucortNot Available
Brand mixturesNot Available
Categories
UNII20O93L6F9H
CAS number196618-13-0
WeightAverage: 312.4045
Monoisotopic: 312.204907394
Chemical FormulaC16H28N2O4
InChI KeyVSZGPKBBMSAYNT-RRFJBIMHSA-N
InChI
InChI=1S/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1
IUPAC Name
ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
SMILES
CCOC(=O)C1=C[C@@H](OC(CC)CC)[[email protected]](NC(C)=O)[C@@H](N)C1
Pharmacology
Indication

Oseltamivir (Tamiflu) is for the treatment of uncomplicated acute illness due to influenza infection in patients 1 year and older who have been symptomatic for no more than 2 days. It is also used for the prophylaxis of influenza in adult patients and adolescents 13 years and older.

Structured Indications
Pharmacodynamics

Oseltamivir is an antiviral drug, a neuraminidase inhibitor used in the treatment and prophylaxis of both influenza A and influenza B. Oseltamivir is a prodrug (usually administered as phosphate), it is hydrolysed hepatically to the active metabolite, the free carboxylate of oseltamivir (GS4071). Like zanamivir, oseltamivir acts as a transition-state analogue inhibitor of influenza neuraminidase.

Mechanism of action

Oseltamivir is an ethyl ester prodrug requiring ester hydrolysis for conversion to the active form, oseltamivir carboxylate. The proposed mechanism of action of oseltamivir is inhibition of influenza virus neuraminidase with the possibility of alteration of virus particle aggregation and release.

TargetKindPharmacological actionActionsOrganismUniProt ID
NeuraminidaseProteinyes
inhibitor
Influenza A virus (strain A/Chile/1/1983 H1N1)P11485 details
Liver carboxylesterase 1Proteinyes
other
HumanP23141 details
Sialidase-1Proteinunknown
inhibitor
HumanQ99519 details
Sialidase-2Proteinunknown
inhibitor
HumanQ9Y3R4 details
Related Articles
Absorption

Readily absorbed from the gastrointestinal tract after oral administration with a bioavailability of 75%.

Volume of distribution
  • 23 to 26 L
Protein binding

Oseltamivir carboxylate: low (3%), Oseltamivir free base: 42%.

Metabolism

Extensively converted to oseltamivir carboxylate by esterases located predominantly in the liver. Neither oseltamivir nor oseltamivir carboxylate is a substrate for, or inhibitor of, cytochrome P450 isoforms. At least 75% of an oral dose reaches the systemic circulation as oseltamivir carboxylate.

Route of elimination

Absorbed oseltamivir is primarily (>90%) eliminated by conversion to oseltamivir carboxylate. Oseltamivir carboxylate is not further metabolized and is eliminated in the urine. Oseltamivir carboxylate is eliminated entirely (>99%) by renal excretion.

Half life

1 to 3 hours in most subjects after oral administration.

ClearanceNot Available
Toxicity

At present, there has been no experience with overdose. Single doses of up to 1000 mg of oseltamivir have been associated with nausea and/or vomiting. Mean LD (intravenous, mouse) = 100 mg/kg.

Affected organisms
  • Influenza Virus
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
ProbenecidThe serum concentration of the active metabolites of Oseltamivir can be increased when Oseltamivir is used in combination with Probenecid.Approved
Food Interactions
  • Take without regard to meals. Food may improve gastric tolerance.
References
Synthesis ReferenceUS5763483
General References
  1. Chokephaibulkit K, Uiprasertkul M, Puthavathana P, Chearskul P, Auewarakul P, Dowell SF, Vanprapar N: A child with avian influenza A (H5N1) infection. Pediatr Infect Dis J. 2005 Feb;24(2):162-6. [PubMed:15702046 ]
  2. de Jong MD, Tran TT, Truong HK, Vo MH, Smith GJ, Nguyen VC, Bach VC, Phan TQ, Do QH, Guan Y, Peiris JS, Tran TH, Farrar J: Oseltamivir resistance during treatment of influenza A (H5N1) infection. N Engl J Med. 2005 Dec 22;353(25):2667-72. [PubMed:16371632 ]
  3. Kiso M, Mitamura K, Sakai-Tagawa Y, Shiraishi K, Kawakami C, Kimura K, Hayden FG, Sugaya N, Kawaoka Y: Resistant influenza A viruses in children treated with oseltamivir: descriptive study. Lancet. 2004 Aug 28-Sep 3;364(9436):759-65. [PubMed:15337401 ]
  4. Ward P, Small I, Smith J, Suter P, Dutkowski R: Oseltamivir (Tamiflu) and its potential for use in the event of an influenza pandemic. J Antimicrob Chemother. 2005 Feb;55 Suppl 1:i5-i21. [PubMed:15709056 ]
External Links
ATC CodesJ05AH02 — Oseltamivir
AHFS Codes
  • 08:18.28
PDB EntriesNot Available
FDA labelDownload (67.2 KB)
MSDSDownload (107 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentInfluenza in Humans1
1CompletedNot AvailableHealthy Volunteers4
1CompletedBasic ScienceDrug Interactions1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedHealth Services ResearchAvian Influenza A Virus1
1CompletedOtherInfluenza, Human1
1CompletedTreatmentEnd Stage Renal Disease (ESRD)1
1CompletedTreatmentFlu caused by Influenza2
1CompletedTreatmentFlu caused by Influenza / Virus Diseases1
1CompletedTreatmentHealthy Volunteers5
1CompletedTreatmentHealthy Volunteers / Influenza A, Influenza B1
1RecruitingTreatmentFlu caused by Influenza1
1TerminatedTreatmentFlu caused by Influenza1
1Unknown StatusPreventionFlu caused by Influenza / Pulmonary Diseases1
1WithdrawnBasic ScienceFlu caused by Influenza / Pregnancy1
1WithdrawnTreatmentHealthy Volunteers1
1, 2CompletedNot AvailableBMI >30 kg/m21
1, 2CompletedTreatmentFlu caused by Influenza3
1, 2RecruitingTreatmentFlu caused by Influenza1
2CompletedOtherHealthy Volunteers1
2CompletedPreventionFlu caused by Influenza1
2CompletedTreatmentFlu caused by Influenza3
2CompletedTreatmentFlu caused by Influenza / Influenza, Avian / Severe Influenza1
2CompletedTreatmentInfluenza A Virus1
2CompletedTreatmentInfluenza A Virus Infection1
2CompletedTreatmentVirus Diseases1
2Not Yet RecruitingTreatmentEpidemic Influenza1
2Not Yet RecruitingTreatmentFocus of Study / Thrombocytopenias1
2RecruitingTreatmentFlu caused by Influenza1
2RecruitingTreatmentInfluenza A Virus Infection1
2RecruitingTreatmentVirus Diseases1
2TerminatedTreatmentInfluenza A Infection1
2TerminatedTreatmentInfluenza A Virus1
2WithdrawnTreatmentFlu caused by Influenza1
2WithdrawnTreatmentInfluenza - Type A Strains1
2, 3WithdrawnTreatmentFlu caused by Influenza1
3CompletedTreatmentFlu caused by Influenza4
3CompletedTreatmentFlu caused by Influenza / Influenza, Human1
3CompletedTreatmentFlu caused by Influenza / Lower Respiratory Tract Infection (LRTI) / Pneumonia / Upper Respiratory Tract Infections / Viral Shedding1
3CompletedTreatmentInfluenza, Human2
3Not Yet RecruitingTreatmentFlu caused by Influenza1
3RecruitingTreatmentFlu caused by Influenza2
3RecruitingTreatmentInfluenza, Human1
3TerminatedTreatmentFlu caused by Influenza / Upper Respiratory Tract Infections1
3TerminatedTreatmentGastric Influenza1
4CompletedNot AvailableDrug Therapy, Combination1
4CompletedNot AvailableFlu caused by Influenza1
4CompletedBasic ScienceFlu caused by Influenza1
4CompletedPreventionFlu caused by Influenza4
4CompletedTreatmentFlu caused by Influenza3
4CompletedTreatmentFlu caused by Influenza / Pneumonia1
4CompletedTreatmentFlu caused by Influenza / Respiratory Tract Infections (RTI)1
4Not Yet RecruitingPreventionFlu caused by Influenza1
4RecruitingTreatmentFlu caused by Influenza3
4TerminatedHealth Services ResearchFlu caused by Influenza1
4TerminatedTreatmentFlu caused by Influenza2
4TerminatedTreatmentFlu caused by Influenza / Influenza, Human1
4Unknown StatusBasic ScienceMetabolic Diseases1
4Unknown StatusPreventionFlu caused by Influenza1
4Unknown StatusTreatmentFlu caused by Influenza1
Not AvailableCompletedNot AvailableFlu caused by Influenza1
Not AvailableCompletedNot AvailablePrematurity of Fetus1
Not AvailableCompletedTreatmentFlu caused by Influenza1
Not AvailableCompletedTreatmentInfluenza A Virus Infection1
Not AvailableRecruitingNot AvailableAcute Bacterial Exacerbation of Chronic Bronchitis (ABECB) / Acute Bacterial Sinusitis (ABS) / Acute Decompensated Heart Failure (ADHF) / Acute Pyelonephritis / Adenovirus / Adjunct to general anesthesia therapy / Adrenal Insufficiency / Airway Swelling / Anaesthesia therapy / Anxiolysis / Arterial Hypotension / Autism, Early Infantile / Autistic Disorder / Bartonellosis / Benzodiazepine Withdrawal / Benzodiazepines / Bipolar Disorder (BD) / Bloodstream Infections / Bone and Joint Infections / Brain Swelling / Bronchospasm / Brucellosis / Cardiac Arrest / Central Nervous System Infections / Cholera / Chronic Bacterial Prostatitis / Community Acquired Pneumonia (CAP) / Complicated Urinary Tract Infections / Convulsions / Cyanide Poisoning / Cytomegalovirus Retinitis / Drug hypersensitivity reaction / Early-onset Schizophrenia Spectrum Disorders / Edema / Epilepsies / Feeling Anxious / Flu caused by Influenza / Gastroparesis / GYNAECOLOGICAL INFECTION / Headaches / Herpes Simplex Virus / Hospital-acquired bacterial pneumonia / Hypercholesterolaemia / Hyperlipidemias / Hypertensive / Infantile Hemangiomas / Infection NOS / Inflammatory Conditions / Inflammatory Reaction / Influenza Treatment or Prophylaxis / Inhalational Anthrax (Post-Exposure) / Intra-Abdominal Infections / Life-threatening Fungal Infections / Lower Respiratory Tract Infection (LRTI) / Meningitis, Bacterial / Migraines / Muscle Spasms / Nausea / Opioid Addiction / Pain / Plague / Pneumonia / Prophylaxis / Psittacosis / Q Fever / Reflux / Relapsing Fever / Rocky Mountain Spotted Fever / Schizophrenic Disorders / Sedation therapy / Seizures / Sepsis / Skeletal Muscle Spasms / Skin and Subcutaneous Tissue Bacterial Infections / Skin Structures and Soft Tissue Infections / Stable Angina (SA) / Thromboprophylaxis / Thrombosis / Trachoma / Treatment-resistant Schizophrenia / Tularemia / Typhus Fever / Uncomplicated Skin and Skin Structure Infections / Uncomplicated Urinary Tract Infections / Urinary Tract Infections (UTIs) / Vomiting / Withdrawal1
Not AvailableRecruitingTreatmentInfluenza, Human1
Not AvailableWithdrawnBasic ScienceInfluenza A Virus Infection / Influenza B Virus Infection1
Pharmacoeconomics
Manufacturers
  • Hoffmann la roche inc
Packagers
Dosage forms
FormRouteStrength
CapsuleOral30 mg/1
CapsuleOral30 mg
CapsuleOral45 mg
CapsuleOral45 mg/1
CapsuleOral75 mg/1
Powder, for suspensionOral12 mg/mL
Powder, for suspensionOral6 mg
Powder, for suspensionOral6 mg/mL
CapsuleOral75 mg
Powder, for suspensionOral12 mg
Prices
Unit descriptionCostUnit
Tamiflu 10 30 mg capsule Box101.54USD box
Tamiflu 10 45 mg capsule Box101.54USD box
Tamiflu 10 75 mg capsule Disp Pack101.54USD disp
Tamiflu 12 mg/ml Suspension51.0USD bottle
Tamiflu 30 mg gel capsule9.76USD gel capsule
Tamiflu 45 mg gel capsule9.76USD gel capsule
Tamiflu 75 mg gel capsule9.76USD gel capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2188835 No2006-08-082016-02-26Canada
US5763483 Yes1997-02-232017-02-23Us
US5866601 Yes1996-08-022016-08-02Us
US5952375 Yes1995-08-272015-08-27Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilitySolubleNot Available
logP1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.686 mg/mLALOGPS
logP1.3ALOGPS
logP1.16ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)14.03ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area90.65 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity84.2 m3·mol-1ChemAxon
Polarizability34.65 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9156
Blood Brain Barrier-0.9535
Caco-2 permeable-0.702
P-glycoprotein substrateSubstrate0.5919
P-glycoprotein inhibitor INon-inhibitor0.5415
P-glycoprotein inhibitor IINon-inhibitor0.9771
Renal organic cation transporterNon-inhibitor0.9429
CYP450 2C9 substrateNon-substrate0.9083
CYP450 2D6 substrateNon-substrate0.8276
CYP450 3A4 substrateSubstrate0.5283
CYP450 1A2 substrateNon-inhibitor0.8367
CYP450 2C9 inhibitorNon-inhibitor0.8774
CYP450 2D6 inhibitorNon-inhibitor0.9174
CYP450 2C19 inhibitorNon-inhibitor0.6677
CYP450 3A4 inhibitorNon-inhibitor0.8364
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testNon AMES toxic0.6907
CarcinogenicityNon-carcinogens0.8863
BiodegradationNot ready biodegradable0.6191
Rat acute toxicity2.2695 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9826
hERG inhibition (predictor II)Non-inhibitor0.9464
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01t9-0193000000-f5d60d35ef59bb0d3d88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0930000000-4bafe71e1cfce532c69eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-b47b81a2da926f1b38a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01bi-0900000000-e54a66b05b36ac125c76View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00dr-0900000000-a088a5ae7a49e423f645View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-a4689c9d2708c9864683View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-07fr-0393000000-c4ca6313b8a95857501fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0920000000-274bd00e87c126ea0431View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-1900000000-ab2b530339386266bb5eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00y3-3900000000-503de5f1484e1733b933View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-006x-6900000000-c732121f239f135b134cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-006x-9600000000-414288f436e77a96401fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-07fr-0393000000-782bc585f56c5193cc4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0920000000-2a6c0c1f08190d6bbc0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-1900000000-3ea178c0a288c37e3e79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00y3-3900000000-0c790adae380f41f557aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-006x-6900000000-793d9a5e1ce9de381e4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-006x-9600000000-ebf8dd7bcfb3a4844078View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-f5e9b54d2909b3aff88dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma amino acids and derivatives
Alternative ParentsEnoate esters / Acetamides / Secondary carboxylic acid amides / Monocarboxylic acids and derivatives / Dialkyl ethers / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
SubstituentsGamma amino acid or derivatives / Enoate ester / Acetamide / Alpha,beta-unsaturated carboxylic ester / Carboxamide group / Carboxylic acid ester / Secondary carboxylic acid amide / Dialkyl ether / Ether / Monocarboxylic acid or derivatives
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptorsdiester, primary amino compound, acetamides, amino acid ester, cyclohexenecarboxylate ester (CHEBI:7798 )

Targets

Kind
Protein
Organism
Influenza A virus (strain A/Chile/1/1983 H1N1)
Pharmacological action
yes
Actions
inhibitor
General Function:
Metal ion binding
Specific Function:
Catalyzes the removal of terminal sialic acid residues from viral and cellular glycoconjugates. Cleaves off the terminal sialic acids on the glycosylated HA during virus budding to facilitate virus release. Additionally helps virus spread through the circulation by further removing sialic acids from the cell surface. These cleavages prevent self-aggregation and ensure the efficient spread of th...
Gene Name:
NA
Uniprot ID:
P11485
Molecular Weight:
51874.045 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. McKimm-Breschkin J, Trivedi T, Hampson A, Hay A, Klimov A, Tashiro M, Hayden F, Zambon M: Neuraminidase sequence analysis and susceptibilities of influenza virus clinical isolates to zanamivir and oseltamivir. Antimicrob Agents Chemother. 2003 Jul;47(7):2264-72. [PubMed:12821478 ]
  4. Du QS, Wang SQ, Chou KC: Analogue inhibitors by modifying oseltamivir based on the crystal neuraminidase structure for treating drug-resistant H5N1 virus. Biochem Biophys Res Commun. 2007 Oct 19;362(2):525-31. Epub 2007 Aug 13. [PubMed:17707775 ]
  5. Wang MZ, Tai CY, Mendel DB: Mechanism by which mutations at his274 alter sensitivity of influenza a virus n1 neuraminidase to oseltamivir carboxylate and zanamivir. Antimicrob Agents Chemother. 2002 Dec;46(12):3809-16. [PubMed:12435681 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
other
General Function:
Triglyceride lipase activity
Specific Function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity,...
Gene Name:
CES1
Uniprot ID:
P23141
Molecular Weight:
62520.62 Da
References
  1. Shi D, Yang J, Yang D, LeCluyse EL, Black C, You L, Akhlaghi F, Yan B: Anti-influenza prodrug oseltamivir is activated by carboxylesterase human carboxylesterase 1, and the activation is inhibited by antiplatelet agent clopidogrel. J Pharmacol Exp Ther. 2006 Dec;319(3):1477-84. Epub 2006 Sep 11. [PubMed:16966469 ]
  2. Wattanagoon Y, Stepniewska K, Lindegardh N, Pukrittayakamee S, Silachamroon U, Piyaphanee W, Singtoroj T, Hanpithakpong W, Davies G, Tarning J, Pongtavornpinyo W, Fukuda C, Singhasivanon P, Day NP, White NJ: Pharmacokinetics of high-dose oseltamivir in healthy volunteers. Antimicrob Agents Chemother. 2009 Mar;53(3):945-52. doi: 10.1128/AAC.00588-08. Epub 2008 Dec 22. [PubMed:19104028 ]
  3. Zhu HJ, Markowitz JS: Activation of the antiviral prodrug oseltamivir is impaired by two newly identified carboxylesterase 1 variants. Drug Metab Dispos. 2009 Feb;37(2):264-7. doi: 10.1124/dmd.108.024943. Epub 2008 Nov 20. [PubMed:19022936 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Exo-alpha-sialidase activity
Specific Function:
Catalyzes the removal of sialic acid (N-acetylneuraminic acid) moities from glycoproteins and glycolipids. To be active, it is strictly dependent on its presence in the multienzyme complex. Appears to have a preference for alpha 2-3 and alpha 2-6 sialyl linkage.
Gene Name:
NEU1
Uniprot ID:
Q99519
Molecular Weight:
45466.96 Da
References
  1. Chavas LM, Kato R, Suzuki N, von Itzstein M, Mann MC, Thomson RJ, Dyason JC, McKimm-Breschkin J, Fusi P, Tringali C, Venerando B, Tettamanti G, Monti E, Wakatsuki S: Complexity in influenza virus targeted drug design: interaction with human sialidases. J Med Chem. 2010 Apr 8;53(7):2998-3002. doi: 10.1021/jm100078r. [PubMed:20222714 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Exo-alpha-(2->8)-sialidase activity
Specific Function:
Catalyzes the removal of sialic acid (N-acetylneuraminic acid) moities from glycoproteins, oligosaccharides and gangliosides.
Gene Name:
NEU2
Uniprot ID:
Q9Y3R4
Molecular Weight:
42253.345 Da
References
  1. Chavas LM, Kato R, Suzuki N, von Itzstein M, Mann MC, Thomson RJ, Dyason JC, McKimm-Breschkin J, Fusi P, Tringali C, Venerando B, Tettamanti G, Monti E, Wakatsuki S: Complexity in influenza virus targeted drug design: interaction with human sialidases. J Med Chem. 2010 Apr 8;53(7):2998-3002. doi: 10.1021/jm100078r. [PubMed:20222714 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Atpase activity, coupled to transmembrane movement of substances
Specific Function:
May be an organic anion pump relevant to cellular detoxification.
Gene Name:
ABCC4
Uniprot ID:
O15439
Molecular Weight:
149525.33 Da
References
  1. Ose A, Ito M, Kusuhara H, Yamatsugu K, Kanai M, Shibasaki M, Hosokawa M, Schuetz JD, Sugiyama Y: Limited brain distribution of [3R,4R,5S]-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate phosphate (Ro 64-0802), a pharmacologically active form of oseltamivir, by active efflux across the blood-brain barrier mediated by organic anion transporter 3 (Oat3/Slc22a8) and multidrug resistance-associated protein 4 (Mrp4/Abcc4). Drug Metab Dispos. 2009 Feb;37(2):315-21. doi: 10.1124/dmd.108.024018. Epub 2008 Nov 24. [PubMed:19029202 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
References
  1. Ogihara T, Kano T, Wagatsuma T, Wada S, Yabuuchi H, Enomoto S, Morimoto K, Shirasaka Y, Kobayashi S, Tamai I: Oseltamivir (tamiflu) is a substrate of peptide transporter 1. Drug Metab Dispos. 2009 Aug;37(8):1676-81. doi: 10.1124/dmd.109.026922. Epub 2009 May 13. [PubMed:19439487 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
References
  1. Ose A, Ito M, Kusuhara H, Yamatsugu K, Kanai M, Shibasaki M, Hosokawa M, Schuetz JD, Sugiyama Y: Limited brain distribution of [3R,4R,5S]-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate phosphate (Ro 64-0802), a pharmacologically active form of oseltamivir, by active efflux across the blood-brain barrier mediated by organic anion transporter 3 (Oat3/Slc22a8) and multidrug resistance-associated protein 4 (Mrp4/Abcc4). Drug Metab Dispos. 2009 Feb;37(2):315-21. doi: 10.1124/dmd.108.024018. Epub 2008 Nov 24. [PubMed:19029202 ]
Drug created on June 13, 2005 07:24 / Updated on July 20, 2017 14:51